Vacation rentals in Shirley

4.87 out of 5 average rating, 151 reviews

A bright living room area features a sectional sofa and a coffee table set on light carpet. A smart TV is positioned on a low stand, and natural light enters through a skylight. Decorative curtains frame the window, adding a touch of style.

Apartment in Medford

Cozy Apartment with King Bed - Separate Entrance

Enjoy your stay in this private, clean and comfy environment. Space offers a bedroom with a king size bed and a desk for at-home work. Living room includes a smart TV and a sectional. Unleash your inner chef! Access to kitchen utensils, dinnerware, and pots/pans. Free parking on premises. Convenient location with many necessities nearby (mall/gas station/restaurants). We are located 2 mins from I-495 and 15 mins from Macarthur airport. Great for visiting family in Port Jefferson, Patchogue, etc!

Apartment in Mastic Beach

A light-filled dining area is highlighted by a white table and two matching chairs. A bowl rests on the table, and sunlight filters through a large window, showcasing views of the green yard outside. Neutral curtains frame the window.

4.66 out of 5 average rating, 88 reviews

Private Cottage

A large rustic apartment space with lots of windows that open a view to the garden. The place is cozy and comfortable with high ceiling and dark laminate wood floor including full bath with a tub and fully equipped kitchenette. A quiet and private suite with private entrance. Charcoal BBQ-grille, outdoor swing, lots of trees and grass Near beach, Wildlife refuge and hiking paths. A 5-minute drive to a Chinese restaurant and a sushi place, Chipotle, an excellent Chicken hotspot and food markets.

4.98 out of 5 average rating, 222 reviews

An expansive deck offers a view of the Great South Bay, with a mix of comfortable seating options, including lounge chairs and a sectional sofa. The area is complemented by manicured green grass and a wooden railing, providing a serene backdrop for outdoor relaxation.

Home in Shirley

Luxurious Waterfront Beach House On The Bay

Relax and enjoy your time at this beautiful east end waterfront getaway. This house is located right on the relaxing and exclusive Great South Bay with private beach... The experience will bring you the feel of tranquility everyone desires with vacationing out east. While offering all the enjoyments the island has at your fingertips. Centrally located to all island destinations. 90 minutes from Manhattan - 15 minutes to West Hampton - 15 minutes to Fire Island Ferrys. Visit top winery’s WiFi

4.87 out of 5 average rating, 230 reviews

A living area features a gray futon adorned with decorative pillows, complemented by a small coffee table. A red accent chair provides additional seating. Soft lighting from the ceiling enhances the space, while wall art depicts blooming flowers, contributing to a welcoming atmosphere.

Apartment in Patchogue

Private 1br Apartment on Long Island

Bright & clean 1br apartment with private entrance on a quiet street. Refrigerator, microwave, keurig incl 2 miles to downtown restaurants, bars, breweries, shopping 10 miles to winery & vineyards 3 miles to beaches 3 miles to Fire Island Ferry 30miles to NYC 3 miles to Baseball Heaven 10 miles to Stonybrook University & hospital 1 mile to public horse farm & stable 3 miles to St Joseph's College .5 mile to Long Island Community Hospital 1 mile to hiking 45min to JFK 10min to McArthur airport

4.84 out of 5 average rating, 55 reviews

An open-concept living area is showcased with a light gray sofa adorned with patterned pillows. A plush area rug lies beneath it, while wooden cabinets and essential appliances are visible in the kitchenette area, complemented by a patterned floor mat.

Home in Shirley

Home Sweet Home by the Beach

Welcome to your cozy retreat on Eastern Long Island. This charming basement apartment is separated and private from the rest of the home. As you enter the backyard you'll see a small patio with a table and 2 chairs. The apartment has an open-concept living area and kitchenette. Just beyond the living area is a full bathroom and spacious bedroom with a Roku TV. Attractions include Smith Point Beach (5 min), Shopping at Tanger Outlet (15 min) and local restaurants. Easy access to NY-27 & 495.

Apartment in Center Moriches

An open studio space features a spacious bed with a light duvet and decorative pillows. A leather couch complements the area, while large windows provide natural light, framed by white blinds. A bedside table and warm lighting create a cozy ambiance.

4.86 out of 5 average rating, 95 reviews

Quiet and comfy studio near the Hamptons

*If you have good prior reviews book our place and receive an offer within 24hrs! A well equipped cozy studio only 20 minutes from the Hamptons and 10 minutes away from LIRR train station to go into NYC (free parking at the train station!) This studio has a small kitchenette to warm up meals, a full size fridge, we include some snacks for those late night cravings. A queen size bed, a separate desk and chair to study or work, a couch, smart TV, and a peaceful environment to relax and unwind.

4.94 out of 5 average rating, 69 reviews

An aerial view showcases a spacious outdoor area featuring a heated pool, hot tub, and multiple seating arrangements. A patio dining table accommodates ten, while lounge chairs surround a fire pit. String lights illuminate the space, enhancing the inviting atmosphere for relaxation and entertainment.

Home in Shirley

Beach Getaway w/ Heated Pool & Hot tub

Long term bookings for are welcome! Discounts for longer stays. Inquire within. Hot tub open year round! Heated pool open May-Sept Take advantage of everything Long Island has to offer! Have fun with the whole family at this stylish custom designed home with plenty of activities to go around. Just a short drive away from beautiful Smith Point Beach, Hamptons, Breweries, Wineries, etc. or relax at home in the pool, hot tub, shooting pool, playing board games, or enjoying movies and music!

4.85 out of 5 average rating, 179 reviews

A spacious living area features large glass windows that frame a stunning sunset over the water. The open design enhances natural light, illuminating the room's elegant furnishings and wooden accents. A dining table is positioned near the windows, inviting relaxed meals with a view.

Cabin in Shirley

A-Frame cabin with private beach & epic sunsets

Just a 1.5 hour drive from NYC, this home is the perfect beach getaway spot, with a few steps from the deck to the private beach with its beautiful view across the Great South Bay. Remote work with stunning water views through the wall of windows & in cold weather light a fire while sunlight floods the living space. Two queen bedrooms & bunk bed room sleeps 6 guests, great for families or a small gathering of friends. 5 min drive to ocean beach with great swimming & surfing at Smith Point.

4.97 out of 5 average rating, 200 reviews

An aerial view captures a private guest house surrounded by lush green landscaping. Outdoor furniture is arranged around a small table, complemented by two sun beds. A barbeque grill is visible near the house, with vibrant flowers accentuating the backyard space.

Home in Brookhaven

Beautiful & Independent Guest House near the water

Welcome to our beautiful yet very private guest house in Brookhaven. You are walking distance from the Deer Run Farm (fresh eggs every morning), Post-Morrow Nature Trails and a short drive to Bellport Village Historic District. We are also very close to Wine Country, The Hamptons & Fire Island. We offer all the accommodations you might need for longer stays Washer & Dryer; Dishwasher; High Speed internet and TVs with all the premium channels. EV Charger available (Tesla - Fees applies).

4.94 out of 5 average rating, 127 reviews

A cozy living area features a plush gray couch adorned with decorative pillows. Vibrant blue walls complement the stylish kitchen cabinetry in the background. A large flat-screen television displays a scenic beach image, while a sleek desk sits nearby. Soft lighting adds to the inviting ambiance.

Apartment in Shirley

Boho Beach Vibez Retreat! Private entrance

"Experience a different kind of stay with our unique Airbnb, the 'Boho Beach Vibez” This cozy 1-bedroom apartment , that’s approximately 500sqft is situated on the first level of our home with a separate entrance . Located in a prime area of our town, you'll find yourself just minutes away from all the stores, restaurants, highways, and within walking distance of hiking trails, the Carman’s river, and 5 miles from Smith Point beach. NOTE : hosts live on top level .

4.94 out of 5 average rating, 250 reviews

A spacious living area displays rustic log walls and a mix of wooden and upholstered furniture. A comfortable leather sofa is positioned near a stone wood stove, while a colorful armchair adds charm. Natural light fills the room through windows adorned with patterned curtains.

Cottage in Patchogue

Quaint Cottage on Long Island's South Shore.

The Cottage is a lovely space enclosed in hedges for privacy on a one acre property. I do have 3 dogs, they are kept in a separate gated area on the property. The cottage is located 3 miles from downtown Patchogue which is enjoying a renaissance. There are many restaurants and cultural activities as well as ferry access to Fire Island (Davis Park) in the warmer weather. We are also the "Gateway" to The Hamptons.

4.54 out of 5 average rating, 170 reviews

A quaint cottage exterior is framed by lush greenery, including ornamental grasses and shrubs. A wooden path leads to the entry, highlighting a welcoming entrance set under a tree. The soft colors of the cottage blend harmoniously with the natural surroundings.

Home in Mastic Beach

Cottage with Seashells

Away from traffic and street noice, this cottage provides a peacefull setting with birds and tree lined streets. You can hear the Montauk train line and bay bridge blowing the horns. Very green, marsh areas along the bay shore line. If the wind is right you can hear the ocean one mile away.

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Popular amenities for Shirley vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Shirley

4.82 out of 5 average rating, 119 reviews

Private room in Mastic

Room #1

Private room in The Hamptons

4.93 out of 5 average rating, 105 reviews

Private Room WHB, Best Location + Price +Superhost

4.94 out of 5 average rating, 126 reviews

A spacious room features a queen-size bed adorned with a light gray quilt. Bedside tables with lamps flank either side, and a decorative bench sits at the foot of the bed. Natural light filters through the sheer curtains, enhancing the calming color palette.

Apartment in North Fork

J&J's BnB Lovely, BR/Bath w/ Private Entrance!

5 out of 5 average rating, 20 reviews

A well-appointed bedroom features soft green walls accented by framed artwork. A spacious bed is dressed in light bedding, complemented by a blue throw. A white lamp sits on a decorative nightstand, and curtains frame a window, providing a serene atmosphere.

Private room in Shirley

Cozy Room Close to the Beach

Private room in Lake Ronkonkoma

4.76 out of 5 average rating, 242 reviews

Convenient and Cozy Location

Private room in Lake Ronkonkoma

A serene bedroom is depicted, featuring a spacious bed adorned with patterned bedding in shades of green. A nightstand with a lamp is positioned alongside the bed. Natural light filters through a window dressed with soft curtains, contributing to a calm atmosphere.

4.93 out of 5 average rating, 222 reviews

Welcome!

4.93 out of 5 average rating, 154 reviews

Private room in Medford

Super quiet and safe place! (Thomas)